期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2013, 期 5, 页码 998-1008出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201271
关键词
Heterogeneous catalysis; Green chemistry; Radical reactions; Radical ions; Electron transfer; Alkylation
资金
- Conicet-Argentina
- Agencia Nacional de Promocion Cientifica y Tecnica, Argentina (PICTO-CRUP) [30891]
The photoinduced electron transfer (PET) substitution reaction of electron-rich aromatic nuclei with perfluoroalkyl R-f groups was carried out in water or aqueous mixtures to render substitution products resulting from replacement of aromatic H atoms with the Rf moiety in good yields (5788%). Some mechanistic aspects are discussed, supporting the notion of a PET reaction leading to a classical radical homolytic aromatic substitution (HAS) followed by an electron transfer (ET) and then a proton transfer (PT) sequence. A radical mechanism superimposed on a redox process is proposed to account for product formation. Evidence for the radical cation species (as an initiation event) generated from electron-rich arenes in the presence of perfluoroalkyl halides is provided by the UV/Vis transient spectra obtained by Nanosecond Laser Flash Photolysis techniques.
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